I've definitely seen the "why do I have to pay to store my files now?" friction play out in this situation.

Some of my relatives are highly anti-cloud. I know they're also at risk to lose their data, as they don't back up anything. When I set up a backup the workflow isn't followed, the time machine drive gets unplugged, etc.

My other set of relatives recognize the concept that they are paying for someone else to handle this data for them and not have to worry about it. They're on the 50GB iCloud plan, so it's not a huge deal.

As far as paying a lot or not a lot, I think it's just a personal question of "is this data important or not?" It either is or isn't. The avenues for saving money if you really want to keep storing a lot of stuff are limited. I should know, I have my own home NAS, and I can tell you it definitely hasn't been a money-saving exercise.

I definitely agree that Files is behind the rest and can be a whole lot better.